N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide

Name: N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 616880-14-9
Cat. No. CS-M2303
Purity≥97%
MDL No.MFCD05663876

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide|CS-M2303

Structure of 616880-14-9

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General Information

CAS No. 616880-14-9
Cat. No. CS-M2303
Purity ≥97%
MDL No. MFCD05663876
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₄S
Molecular Weight None
Synonym(s) N-(Methylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine; ; 4-(Methanesulfonylamino)phenylboronic Acid Pinacol Ester
SMILES CS(=O)(NC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1)=O

Description

N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide features a boronate ester group enabling reliable Suzuki-Miyaura cross-coupling reactions. The methanesulfonyl moiety enhances solubility and stability under standard conditions. This compound integrates readily into complex molecular architectures with minimal purification requirements.

Application

N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The stable, air-tolerant boronate ester enables efficient C–C bond formation under mild conditions, while the sulfonamide group provides excellent solubility and functional group compatibility. This reagent facilitates the synthesis of biaryl scaffolds common in medicinal chemistry and materials science, with straightforward purification via standard chromatographic methods.

Synthesis

Route1
- 124-63-0
- In-stock
  
  214360-73-3
- ~92%
- In-stock
  
  616880-14-9
References
- SUGEN, INC. Patent: WO2004/76412 A2, 2004 ; Location in patent: Page 104 ; WO 2004/076412 A2
Route2
- In-stock
  
  4284-50-8
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  616880-14-9
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 20, # 5 p. 1724 - 1727

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 64.63
LogP 1.3573
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide

CAS No. 616880-14-9

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